The photodynamic therapy activity of 3-(1-hydroxylethyl)-3-devinyl-131-(dicyanomethylene) pyropheophorbide-a methyl ester (HDCPPa) against HeLa cell in vitro

Abstract

Photodynamic therapy (PDT) has been a potential therapeutic method for the treatment of various cancers, with photosensitizer being the key component in photodynamic therapy. In this paper, we prepared a photosensitizer 3-(1-hydroxylethyl)-3-devinyl-131-(dicyanomethylene) pyropheophorbide-a methyl ester (HDCPPa), based on chlorophyll pyropheophorbide-a according to the previous report, and systematically investigated the fluorescence emission spectrum and ultraviolet absorption spectrum HDCPPa has long absorption in the near-infrared spectral region (around 695 nm). The excitation wavelength and the emission wavelength were 415 nm and 699 nm respectively in dichloromethane, 1O2 quantum yield was 63.5%. HDCPPa also had high stability in PBS solution, DMEM cell culture medium and normal saline (NS) in vitro. After irradiation by the light of 675 nm (10 J.cm[Formula: see text]) for 70 min the degradation rate of HDCPPa was 12.5%, which indicated that the target compound showed high stability under light. The in vitrophotodynamic therapy activities against HeLa cells were also studied, which showed that HDCPPa had extremely low dark toxicity but great phototoxicity, and the cell viability is lower than 10% under the light irradiation of 675 nm (10 J.cm[Formula: see text]). Moreover, HDCPPa can quickly enter the cell after being incubated with HeLa cells in less than 30 min. We also evaluated the mechanism of the photochemical reaction, which had proved that Type II is primarily responsible for the cell death. Therefore HDCPPa could serve as a very promising photosensitizer for photodynamic therapy.